#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/91/2229120.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229120
loop_
_publ_author_name
'Gurumoorthy, Anuradha'
'Gopalsamy, Vasuki'
'K, Ramamurthi.'
'Piplani, Poonam'
'Malik, Ruchi'
_publ_section_title
;
 N-[4-(2-Morpholinoethoxy)phenyl]acetamide monohydrate
;
_journal_coeditor_code           JH2248
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o262
_journal_paper_doi               10.1107/S1600536810053675
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H20 N2 O3, H2 O'
_chemical_formula_moiety         'C14 H20 N2 O3, H2 O'
_chemical_formula_sum            'C14 H22 N2 O4'
_chemical_formula_weight         282.34
_chemical_name_systematic
;
N-[4-(2-Morpholinoethoxy)phenyl]acetamide monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.572(3)
_cell_angle_beta                 73.326(3)
_cell_angle_gamma                79.876(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0560(3)
_cell_length_b                   10.2859(6)
_cell_length_c                   10.7234(6)
_cell_measurement_temperature    293(2)
_cell_volume                     733.92(7)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       multi-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17239
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  3600
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7052
_exptl_absorpt_correction_T_min  0.6028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0701P)²+0.1005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                2697
_reflns_number_total             3723
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2248.cif
_cod_data_source_block           I
_cod_database_code               2229120
_cod_database_fobs_code          2229120
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -1.0978(2) 0.87498(15) 0.43055(17) 0.0553(4) Uani d . 1 . .
H H1A -1.1906 0.8271 0.4103 0.083 Uiso calc R 1 . .
H H1B -1.0726 0.9451 0.3692 0.083 Uiso calc R 1 . .
H H1C -1.1540 0.9115 0.5169 0.083 Uiso calc R 1 . .
C C2 -0.9045(2) 0.78313(14) 0.42318(14) 0.0469(3) Uani d . 1 . .
C C3 -0.54229(18) 0.74747(11) 0.30094(12) 0.0375(3) Uani d . 1 . .
C C4 -0.47022(19) 0.64413(12) 0.37122(13) 0.0424(3) Uani d . 1 . .
H H4 -0.5557 0.6167 0.4472 0.051 Uiso calc R 1 . .
C C5 -0.27177(19) 0.58104(12) 0.32949(13) 0.0429(3) Uani d . 1 . .
H H5 -0.2246 0.5123 0.3778 0.051 Uiso calc R 1 . .
C C6 -0.14488(19) 0.62023(13) 0.21659(14) 0.0455(3) Uani d . 1 . .
C C7 -0.2163(2) 0.72379(15) 0.14592(15) 0.0541(4) Uani d . 1 . .
H H7 -0.1311 0.7506 0.0696 0.065 Uiso calc R 1 . .
C C8 -0.4117(2) 0.78676(13) 0.18802(14) 0.0465(3) Uani d . 1 . .
H H8 -0.4575 0.8567 0.1403 0.056 Uiso calc R 1 . .
C C9 0.1304(2) 0.45012(14) 0.22585(16) 0.0514(4) Uani d . 1 . .
H H9A 0.0572 0.3790 0.2243 0.062 Uiso calc R 1 . .
H H9B 0.1241 0.4676 0.3152 0.062 Uiso calc R 1 . .
C C10 0.3450(2) 0.41666(14) 0.14270(15) 0.0492(3) Uani d . 1 . .
H H10A 0.3467 0.4195 0.0519 0.059 Uiso calc R 1 . .
H H10B 0.4183 0.4836 0.1564 0.059 Uiso calc R 1 . .
C C11 0.4840(2) 0.28395(14) 0.29775(15) 0.0494(3) Uani d . 1 . .
H H11A 0.3564 0.2987 0.3649 0.059 Uiso calc R 1 . .
H H11B 0.5564 0.3542 0.3040 0.059 Uiso calc R 1 . .
C C12 0.6040(2) 0.15244(16) 0.31893(16) 0.0588(4) Uani d . 1 . .
H H12A 0.6279 0.1526 0.4036 0.071 Uiso calc R 1 . .
H H12B 0.5276 0.0829 0.3180 0.071 Uiso calc R 1 . .
C C13 0.7573(2) 0.12794(15) 0.09625(16) 0.0567(4) Uani d . 1 . .
H H13A 0.6811 0.0594 0.0917 0.068 Uiso calc R 1 . .
H H13B 0.8851 0.1096 0.0296 0.068 Uiso calc R 1 . .
C C14 0.6448(2) 0.25923(15) 0.07117(15) 0.0516(4) Uani d . 1 . .
H H14A 0.7218 0.3279 0.0741 0.062 Uiso calc R 1 . .
H H14B 0.6257 0.2590 -0.0149 0.062 Uiso calc R 1 . .
N N1 -0.74111(16) 0.81708(11) 0.33615(12) 0.0437(3) Uani d . 1 . .
N N2 0.44861(14) 0.28678(10) 0.16958(11) 0.0406(3) Uani d . 1 . .
O O1 -0.89898(17) 0.68586(13) 0.49128(14) 0.0801(4) Uani d . 1 . .
O O3 0.05217(15) 0.56571(11) 0.16672(11) 0.0655(3) Uani d . 1 . .
O O5 0.79129(15) 0.12632(12) 0.22060(12) 0.0651(3) Uani d . 1 . .
O O6 1.21505(19) 0.07084(12) 0.18771(14) 0.0651(3) Uani d . 1 . .
H H1 -0.757(2) 0.8870(18) 0.2907(16) 0.055(4) Uiso d . 1 . .
H H6A 1.095(4) 0.100(2) 0.202(2) 0.081(6) Uiso d . 1 . .
H H6B 1.275(4) 0.138(2) 0.177(2) 0.092(7) Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 N1 . . 123.54(13) ?
O1 C2 C1 . . 121.51(13) ?
N1 C2 C1 . . 114.95(12) ?
C4 C3 C8 . . 118.57(11) ?
C4 C3 N1 . . 124.49(12) ?
C8 C3 N1 . . 116.94(11) ?
C3 C4 C5 . . 120.70(12) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 120.00(12) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
O3 C6 C5 . . 125.00(12) ?
O3 C6 C7 . . 115.48(12) ?
C5 C6 C7 . . 119.51(12) ?
C8 C7 C6 . . 120.36(12) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C7 C8 C3 . . 120.84(12) ?
C7 C8 H8 . . 119.6 ?
C3 C8 H8 . . 119.6 ?
O3 C9 C10 . . 103.45(11) ?
O3 C9 H9A . . 111.1 ?
C10 C9 H9A . . 111.1 ?
O3 C9 H9B . . 111.1 ?
C10 C9 H9B . . 111.1 ?
H9A C9 H9B . . 109.0 ?
N2 C10 C9 . . 113.88(11) ?
N2 C10 H10A . . 108.8 ?
C9 C10 H10A . . 108.8 ?
N2 C10 H10B . . 108.8 ?
C9 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
N2 C11 C12 . . 110.39(12) ?
N2 C11 H11A . . 109.6 ?
C12 C11 H11A . . 109.6 ?
N2 C11 H11B . . 109.6 ?
C12 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
O5 C12 C11 . . 111.16(13) ?
O5 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
O5 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
O5 C13 C14 . . 110.89(13) ?
O5 C13 H13A . . 109.5 ?
C14 C13 H13A . . 109.5 ?
O5 C13 H13B . . 109.5 ?
C14 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.0 ?
N2 C14 C13 . . 110.03(11) ?
N2 C14 H14A . . 109.7 ?
C13 C14 H14A . . 109.7 ?
N2 C14 H14B . . 109.7 ?
C13 C14 H14B . . 109.7 ?
H14A C14 H14B . . 108.2 ?
C2 N1 C3 . . 128.45(11) ?
C2 N1 H1 . . 118.1(11) ?
C3 N1 H1 . . 113.3(11) ?
C11 N2 C10 . . 111.50(11) ?
C11 N2 C14 . . 107.90(11) ?
C10 N2 C14 . . 108.26(10) ?
C6 O3 C9 . . 118.64(10) ?
C13 O5 C12 . . 109.68(11) ?
H6A O6 H6B . . 106(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.5007(19) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 O1 . 1.2151(17) ?
C2 N1 . 1.3483(17) ?
C3 C4 . 1.3851(17) ?
C3 C8 . 1.3883(18) ?
C3 N1 . 1.4103(15) ?
C4 C5 . 1.3884(17) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3760(19) ?
C5 H5 . 0.9300 ?
C6 O3 . 1.3632(15) ?
C6 C7 . 1.3873(18) ?
C7 C8 . 1.3707(18) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 O3 . 1.4236(16) ?
C9 C10 . 1.5079(18) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N2 . 1.4655(16) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 N2 . 1.4638(18) ?
C11 C12 . 1.510(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 O5 . 1.4250(19) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 O5 . 1.420(2) ?
C13 C14 . 1.497(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 N2 . 1.4695(16) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
N1 H1 . 0.860(18) ?
O6 H6A . 0.82(2) ?
O6 H6B . 0.86(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O6 1_365 0.860(18) 2.157(18) 3.0148(17) 174.8(14)
O6 H6A O5 . 0.82(2) 2.06(3) 2.8640(18) 165(2)
O6 H6B N2 3_655 0.86(3) 2.11(2) 2.9586(17) 171(2)
C4 H4 O1 . 0.93 2.32 2.8896(19) 120
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 C3 C4 C5 . . . . -0.1(2) ?
N1 C3 C4 C5 . . . . -179.93(12) ?
C3 C4 C5 C6 . . . . -0.6(2) ?
C4 C5 C6 O3 . . . . 179.86(13) ?
C4 C5 C6 C7 . . . . 0.7(2) ?
O3 C6 C7 C8 . . . . -179.30(14) ?
C5 C6 C7 C8 . . . . 0.0(2) ?
C6 C7 C8 C3 . . . . -0.7(2) ?
C4 C3 C8 C7 . . . . 0.8(2) ?
N1 C3 C8 C7 . . . . -179.40(13) ?
O3 C9 C10 N2 . . . . -169.50(12) ?
N2 C11 C12 O5 . . . . 58.19(16) ?
O5 C13 C14 N2 . . . . -60.57(16) ?
O1 C2 N1 C3 . . . . 4.2(3) ?
C1 C2 N1 C3 . . . . -175.68(13) ?
C4 C3 N1 C2 . . . . -15.1(2) ?
C8 C3 N1 C2 . . . . 165.11(14) ?
C12 C11 N2 C10 . . . . -175.90(11) ?
C12 C11 N2 C14 . . . . -57.14(15) ?
C9 C10 N2 C11 . . . . -68.97(16) ?
C9 C10 N2 C14 . . . . 172.48(13) ?
C13 C14 N2 C11 . . . . 58.35(15) ?
C13 C14 N2 C10 . . . . 179.16(13) ?
C5 C6 O3 C9 . . . . 7.5(2) ?
C7 C6 O3 C9 . . . . -173.29(14) ?
C10 C9 O3 C6 . . . . 177.79(13) ?
C14 C13 O5 C12 . . . . 59.49(16) ?
C11 C12 O5 C13 . . . . -58.19(17) ?
O1 C2 N1 C3 . . . . 4.2(3) ?
C1 C2 N1 C3 . . . . -175.68(13) ?
C2 N1 C3 C4 . . . . -15.1(2) ?
C2 N1 C3 C8 . . . . 165.11(14) ?
C7 C6 O3 C9 . . . . -173.29(14) ?
C5 C6 O3 C9 . . . . 7.5(2) ?
C6 O3 C9 C10 . . . . 177.79(13) ?
O3 C9 C10 N2 . . . . -169.50(12) ?
C9 C10 N2 C11 . . . . -68.97(16) ?
C9 C10 N2 C14 . . . . 172.48(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656474
